HCID 86740456, compound → HCID 86740455, compound

HRID 653279Notes

Reaction equation

HRID 653279 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:35][O:36][CH3:37])[C:8]([NH:10][C@H:11]2[C@@H:14]([CH2:15][NH:16]C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[N:13]([S:30]([O-:33])(=[O:32])=[O:31])[C:12]2=[O:34])=[O:9])[N:6]=1.[Na+].[H][H]>O.O1CCCC1.[Pd]>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:35][O:36][CH3:37])[C:8]([NH:10][C@H:11]2[C@@H:14]([CH2:15][NH2:16])[N:13]([S:30]([OH:33])(=[O:31])=[O:32])[C:12]2=[O:34])=[O:9])[N:6]=1

Participants

6

Reactant 2

HCID 86740456HCID 86740456, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86740455HCID 86740455, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of 15 ml of water and 15 ml of tetrahydrofuran is dissolved 203 mg of sodium cis-3-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-4-(p-nitrobenzyloxycarbonylaminomethyl)-2-oxoazetidine-1-sulfonate (syn-isomer), followed by addition of 190 mg of 10% palladium-on-carbon. The mixture is stirred in a hydrogen atmosphere at room temperature for 3 hours. The catalyst is filtered off and the filtrate is washed with ethyl acetate and concentrated under reduced pressure. The residue is chromatographed on an Amberlite XAD-II column and lyophilized to give a colorless powder. The powder is rechromatographed on a Sephadex LH-20 column and lyophilized to give cis-3-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-4-aminomethyl-2-oxoazetidine-1-sulfonic acid (syn-isomer).

Workup

  1. filtrationThe catalyst is filtered off
  2. washthe filtrate is washed with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is chromatographed on an Amberlite XAD-II column
  5. customto give a colorless powder
  6. customThe powder is rechromatographed on a Sephadex LH-20 column

Sources & evidence

ORD record
ord-4d49df083a2946e99475d70ac97e776e
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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